The long read: Simon Milton reflects on his 30 years with Ipswich Town

Simon Milton at Ipswich Town Football ground
Picture: SEANA HUGHES

Simon Milton at Ipswich Town Football ground Picture: SEANA HUGHES

Simon Milton joined Ipswich Town from Bury Town in 1987. Thirty years on he is leaving Portman Road, to start a new career with shipping company OMA Group, as a Blues legend. CHRIS BRAMMER met him.

Simon Milton stands alongside Ipswich Town manager Mick McCarthy at the club's open day in 2016.

Simon Milton stands alongside Ipswich Town manager Mick McCarthy at the club's open day in 2016. - Credit: Archant

He joined Ipswich Town as an unknown and 30 years later is leaving as a Blues legend.

Simon Milton has to pinch himself when he thinks of what he achieved at Portman Road for 11 years as a player and then for 19 years off the pitch, in a number of vital roles, including his most recent, Director of Academy Sales.

Yet, when the fresh-faced 24-year-old secured his first professional contract with the Blues, gaining iconic status was not part of his plan – Milton, who has gone on to become a prolific and tireless fundraiser for Prostate Cancer, having far more modest aims.

“I just wanted another year,” says Milton, recalling his arrival at Portman Road in August 1987.


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“It’s as simple as that.

“I was playing a good level of football at the time, in non-league, at Bury Town and I signed a one-year deal at Ipswich.

Simon Milton launches the Ipswich Town charity bike ride from London to Amsterdam with Mick McCarth

Simon Milton launches the Ipswich Town charity bike ride from London to Amsterdam with Mick McCarthy (left), Alan Lee and John Reader (right) - Credit: Archant

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“After a month at Ipswich I thought to myself ‘I ain’t going back to Bury’ and that’s no disrespect to Bury but I wanted to be a professional footballer for the rest of my playing career and at the time there were good players coming through, the likes of Jason Dozzell, Micky Stockwell and Chris Kiwomya, (John) Warky coming back – great people that are still friends now.

“To play for 11 seasons, and I look at Micky Stockwell who probably played for 17 seasons, you have got to prove yourself every time a new manager comes in.

“You don’t have to be the best player, but you have to be honest, reliable and you have to be the person he (the manager) can pick.

“That happened after John Duncan, John Lyall and after George (Burley), I managed to stay at the club up until I retired and that is testament to the work you put in.

“When I see someone like Micky Stockwell, who kept working hard and proving himself to people, that’s what it’s all about.”

Such a mentality saw Milton make a successful transition from being a player, to becoming just as vital a cog in the wheel behind the scenes after hanging his boots up,

Simon Milton in action for Town, at Oxford, in 1989

Simon Milton in action for Town, at Oxford, in 1989 - Credit: Archant

So much so that it’s fair to say his achievements off the pitch, especially from a commercial and fundraising point-of-view, are on a par with what he did on it.

“As soon as I finished playing I sat down with the chairman at the time, David Sheepshanks, and worked out a role for me to stay within the club, because that’s what he was offering,” Milton recalls.

“I had just finished playing and had my testimonial year, the academy was just starting, so timing wise it couldn’t have been better for me.

“When the academy started, I always worked with the academy – there was a lot of promotional stuff there – I was working with the Trust for a while and then after administration when Paul Jewell came in I started doing player liaison, looking after players, as well as doing the academy.

“But in the last four or five years we have taken the association, which is the fundraising side of the academy, to a whole new level. I think we have raised over a million pounds during the last five years.

“On top of that it is all the events that we do, the biggest being the charity cycle rides. We have raised over £300,000 for Prostate Cancer, the Ipswich Town charity and various other charities.

Simon Milton in action for Town in the mid-1990s

Simon Milton in action for Town in the mid-1990s

“If there is one thing I am particularly proud of, it would be those (Prostate Cancer) bike rides which have grown year on year. Those events will stay with me and, with the club, I will continue to be involved with them.”

Milton, who was a key member of the 1991-92 Division Two championship-winning team, going on to play in the Premier League for three seasons, added: “The last 30 years have been absolutely amazing, to play for 11 and stay here all that time and to have been involved with so many different players, managers, events.

“Sometimes I forget about my playing career.”

Milton will now enter the third stage of his professional career and is stepping out of his comfort zone, despite having built up the skill set to be able to take on a role away from football comfortably.

Milton is joining shipping company, OMA Group to oversee the company’s Corporate Social Responsibility programme in Ghana.

“I have had to make many decisions in my career and the one to leave what I was doing 30 years ago to become a professional footballer, was the easiest I have ever made,” he admits.

Simon Milton scores a goal for Ipswich at Leeds, in the early days of his Town career.

Simon Milton scores a goal for Ipswich at Leeds, in the early days of his Town career.

“Thirty years later, this is probably the toughest I have ever had to make.”

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